Journal
JOURNAL OF BIOTECHNOLOGY
Volume 125, Issue 3, Pages 311-318Publisher
ELSEVIER SCIENCE BV
DOI: 10.1016/j.jbiotec.2006.03.012
Keywords
Bz-RGDS-NH2; peptide synthesis; lipase; organic solvents
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The tetrapeptide Bz-Arg-Gly-Asp-Ser-NH2 (Bz-RGDS-NH2) was successfully synthesized by a combination of chemical and enzymatic methods in this study. Firstly, the precursor tripeptide Gly-Asp-Ser-NH2 (GDS-NH2) was synthesized by a novel chemical method in four steps including chloroacetylation of L-aspartic acid, synthesis of chloroacetyl L-aspartic acid anhydride, the synthesis of ClCH(2)COAsp-SerOMe and ammonolysis of ClCH(2)COAsp-SerOMe. Secondly, lipase (PPL) was used to catalyze the formation of Bz-RGDS-NH2 in aqueous water-miscible organic cosolvent systems using Bz-Arg-OEt as the acyl donor and GDS-NH2 as the nucleophile. The optimum conditions were Bz-Arg-OEt 50 mM; GDS-NH2 400 mM; 10 degrees C, 0.1 M phosphate buffer, pH 7.5; 60% DMF or 58% DMSO, PPL: 10 mg ml(-1) with the maximum yields of the tetrapeptide of 73.6% for DMF and 70.4% for DMSO, respectively. The secondary hydrolysis of the tetrapeptide product did not take place due to the absence of amidase activity of lipase. (c) 2006 Elsevier B.V. All rights reserved.
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